Citation: Zhao Suyan, Wang Zuli. Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 862-866. doi: 10.6023/cjoc201510027 shu

Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst

Zhao Suyan ^a ,
Wang Zuli ^b,,

a.
a. Jilin Police College Experimental Technology Center, Changchun 130117;
b.
b. College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109

Corresponding author: Wang Zuli,
Received Date: 23 October 2015
Available Online: 16 November 2015
Fund Project: 国家自然科学基金(No.21402103) (No.21402103)山东省优秀中青年基金(No.BS2013YY024) (No.BS2013YY024)中国博士后基金(No.150030)资助项目. (No.150030)

A green and efficient protocol for the synthesis of phenols using recyclable chitosan@copper as catalyst was developed. Phenols can be obtained in moderate to excellent yields. The catalyst can be recycled and reused for five times without significant loss of its catalytic activity.
- chitosan@copper,
- recyclable,
- phenylboronic acid,
- water
1. [1]
  [1] Rappoport, Z. The Chemistry of Phenols, Wiley-VCH, Weinheim,Germany, 2003.
2. [2]
  [2] Zhang, R. X.; Zhang, X. D. Chemical Industry 2008, 26, 47 (in Chinese). (张日新, 张晓东, 化学工业, 2008, 26, 47.)
3. [3]
  [3] (a) Anderson, K. W.; Ikawa, T. R.; Tundel, E. S.; Buchwald, L. J. Am. Chem. Soc.2006, 128, 10694.
4. [4]
  (b) Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402.
5. [5]
  (c) Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595.
6. [6]
  (d) Schulz, T.; Torborg, C.; Schäffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Börner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918.
7. [7]
  (e) Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Angew. Chem., Int. Ed. 2007, 46, 7251.
8. [8]
  (f) Chen, G. S.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2007, 48, 473.
9. [9]
  [4] (a) Yang, D. S.; Fu, H. Chem. Eur. J. 2010, 16, 2366.
10. [10]
  (b) Kormos, C. M.; Leadbeater, N. E. Tetrahedron 2006, 62, 4728;
11. [11]
  (c) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.
12. [12]
  (d) Zhao, D. B.; Wu, N. J.; Zhang, S.; Xi, P.; Su, X. Y.; Lan, J. B.; You, J. S. Angew. Chem., Int. Ed. 2009, 48, 8729.
13. [13]
  [5] Yin, L.; Leibescher, J. Chem. Rev. 2007, 107, 133.
14. [14]
  [6] Li, B.; Li, M.; Yao, C. H.; Shi, Y. F.; Ye, D. R.; Wu, J.; Zhao, D. Y. J. Mater. Chem. 2013, 1, 6742.
15. [15]
  [7] For selected examples, see: (a) Kantam, M. L.; Yadav, Y.; Laha, Y.; Srinivas, P.; Sreedhar, B.; Figueras, F. J. Org. Chem. 2009, 74, 4608.
16. [16]
  (b) Kundu, D.; Chatterjee, T.; Ranu, B. C. Adv. Synth. Catal. 2013, 355, 2285.
17. [17]
  (c) Brahmachari, G.; Laskar, S.; Barik, P. RSC Adv. 2013, 3, 142;
18. [18]
  (d) Parella, R.; Kumar, A; Babu, S. A. Tetrahedron Lett. 2013, 54, 1738.
19. [19]
  (e) Yang, S.; Wu, C.; Zhou, H.; Yang, Y.; Zhao, Y.; Wang, C.; Yang, W.; Xu, J. Adv. Synth. Catal. 2013, 355, 53.
20. [20]
  (f) Swapna, K.; Murthy, S. N.; Jyothi, M. T.; Nageswar, Y. V. D. Org. Biomol. Chem. 2011, 5989.
21. [21]
  (g) Hudson, R.; Ishikawa, S.; Li, C.-J.; Moores, A. Synlett 2013, 1637.
22. [22]
  (h) Dandia, A.; Jain, A. K.; Sharma, S. RSC Adv. 2013, 3, 2924.
23. [23]
  (i) Kumar, A. S.; Reddy, M.; M.Knorn, A.; Reiser, O.; Sreedhar, B. Eur. J. Org. Chem. 2013, 4, 674.
24. [24]
  (j) Wang, Z. L. RSC Adv. 2015, 5, 5563.
25. [25]
  [8] Zhang, J.; Han, D.; Zhang, H.; Chaker, M.; Zhao, Y.; Ma, D. Chem. Commun. 2012, 48, 11510.
26. [26]
  [9] (a) Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Appl. Catal. 2011, 393, 231.
27. [27]
  (b) Lasri, J.; Leod, T. C. O. M.; Pombeiro, A. J. L. Appl. Catal. 2011, 393, 94.
28. [28]
  (c) Yi, S. S.; Lee, D. H.; Sin, E.; Lee, Y. S. Tetrahedron Lett. 2007, 48, 6771.
29. [29]
  [10] (a) Shen, C.; Xu, J.; Yu, W.; Zhang, P. Green Chem. 2014, 16, 3007.
30. [30]
  (b) Shen, C.; Xu, J.; Yu, W. B.; Zhang, P. F. Green Chem. 2014, 16, 3007.
31. [31]
  [11] Yang, B.; Mao, Z. X.; Zhu, X. H.; Wan, Y. Q. Catal. Commun. 2015, 60, 92.
32. [32]
  [12] Pal, M.; Parasuraman, K.; Yeleswarapu, K. R. Org. Lett. 2003, 5, 349.
33. [33]
  [13] Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 623.
34. [34]
  [14] Jiang, M.; Yang, H. J.; Li, Y.; Jia, Z. Y.; Fu, H. Chin. Chem. Lett. 2014, 25, 715.
35. [35]
  [15] Yang, D. S.; An, B. J.; Wei, W.; Jiang, M.; You, J. M.; Wang, H. Tetrahedron 2014, 70, 3630.
36. [36]
  [16] Xu, J. M.; Wang, X. Y.; Shao, C. W.; Su, D. Y.; Cheng, G. L.; Hu, Y. F. Org. Lett. 2010, 12, 164.
37. [37]
  [17] Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.
1. [1]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
2. [2]
  Sumiya Akter Dristy , Md Ahasan Habib , Shusen Lin , Mehedi Hasan Joni , Rutuja Mandavkar , Young-Uk Chung , Md Najibullah , Jihoon Lee . Exploring Zn doped NiBP microspheres as efficient and stable electrocatalyst for industrial-scale water splitting. Acta Physico-Chimica Sinica, 2025, 41(7): 100079-0. doi: 10.1016/j.actphy.2025.100079
3. [3]
  Xi YANG , Chunxiang CHANG , Yingpeng XIE , Yang LI , Yuhui CHEN , Borao WANG , Ludong YI , Zhonghao HAN . Co-catalyst Ni₃N supported Al-doped SrTiO₃: Synthesis and application to hydrogen evolution from photocatalytic water splitting. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 440-452. doi: 10.11862/CJIC.20240371
4. [4]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
5. [5]
  Zhenhuan Wang , Weifei Wei , Ruijie Ma , Dou Luo , Zhanxiang Chen , Jun Zhang , Liyang Yu , Gang Li , Zhenghui Luo . 苯并[a]苯嗪受体的核心氰基化实现高效(19.04%)绿色溶剂加工的二元有机太阳能电池. Acta Physico-Chimica Sinica, 2026, 42(2): 100182-0. doi: 10.1016/j.actphy.2025.100182
6. [6]
  Qingqing SHEN , Xiangbowen DU , Kaicheng QIAN , Zhikang JIN , Zheng FANG , Tong WEI , Renhong LI . Self-supporting Cu/α-FeOOH/foam nickel composite catalyst for efficient hydrogen production by coupling methanol oxidation and water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1953-1964. doi: 10.11862/CJIC.20240028
7. [7]
  Nengmin ZHU , Wenhao ZHU , Xiaoyao YIN , Songzhi ZHENG , Hao LI , Zeyuan WANG , Wenhao WEI , Xuanheng CHEN , Weihai SUN . Preparation of high-performance CsPbBr₃ perovskite solar cells by the aqueous solution solvent method. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1131-1140. doi: 10.11862/CJIC.20240419
8. [8]
  Lingling Li , Zhe Chen . Charge transfer mechanism investigation of S-scheme photocatalyst using soft X-ray absorption spectroscopy. Acta Physico-Chimica Sinica, 2026, 42(4): 100215-0. doi: 10.1016/j.actphy.2025.100215
9. [9]
  Wentao Xu , Xuyan Mo , Yang Zhou , Zuxian Weng , Kunling Mo , Yanhua Wu , Xinlin Jiang , Dan Li , Tangqi Lan , Huan Wen , Fuqin Zheng , Youjun Fan , Wei Chen . Bimetal Leaching Induced Reconstruction of Water Oxidation Electrocatalyst for Enhanced Activity and Stability. Acta Physico-Chimica Sinica, 2024, 40(8): 2308003-0. doi: 10.3866/PKU.WHXB202308003
10. [10]
  Sen Lin , Rong Jiang , Xuefeng Lu , Guohui Jiang , Kaining Ding , Jinshui Zhang , Xinchen Wang . Promoting the Integration of Science and Education through Digital Intelligence Technology: Data-Driven Development of Efficient Water Electrolysis Catalysts in Comprehensive Chemical Experiment Teaching. University Chemistry, 2026, 41(1): 188-203. doi: 10.12461/PKU.DXHX202505090
11. [11]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027
12. [12]
  Meihui Cai , Yi Huang , Xingxing Ma , Qiuling Song . Exploring the Mysteries of the Petasis-Boronic Acid-Mannich Reaction. University Chemistry, 2025, 40(11): 184-190. doi: 10.12461/PKU.DXHX202412054
13. [13]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-Based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-0. doi: 10.3866/PKU.WHXB202406029
14. [14]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
15. [15]
  Haiqiang Lin , Weizheng Weng , Jingdong Lin , Mingshu Chen , Xueming Fang , Lefu Yang . Diverse Variables-Driven Catalytic Optimization: Experimental Enhancement and Instructional Design for Selective Methane Oxidation on Supported Nickel-based Catalysts. University Chemistry, 2025, 40(11): 327-336. doi: 10.12461/PKU.DXHX202505106
16. [16]
  Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
17. [17]
  Dong-Bing Cheng , Junxin Duan , Haiyu Gao . Experimental Teaching Design on Chitosan Extraction and Preparation of Antibacterial Gel. University Chemistry, 2024, 39(2): 330-339. doi: 10.3866/PKU.DXHX202308053
18. [18]
  Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co₃O₄ as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
19. [19]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
20. [20]
  Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO₂ Reduction to C₂₊ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1272)
HTML views(156)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142